Name: 769-78-8|Vinyl benzoate|98% (stabilized with MEHQ)
Brand: Ambeed
SKU: A245108
Price: 15.0 USD
Availability: InStock
Rating: 98 (29 reviews)

1
[ 94-49-5 ]
[ 769-78-8 ]

Yield	Reaction Conditions	Operation in experiment
	at 360 - 425℃;

Reference： [1]Current Patent Assignee: DOW INC - US2251983, 1940, A

2
[ 94-49-5 ]
[ 769-78-8 ]
[ 65-85-0 ]

Yield	Reaction Conditions	Operation in experiment
	at 360 - 425℃;

Reference： [1]Current Patent Assignee: DOW INC - US2251983, 1940, A

3
[ 769-78-8 ]
benzoic acid-(1,2-dichloro-ethyl ester) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With manganese(II) chloride tetrahydrate; 1,1,1,2-tetrachoroethane; N,N,N,N-tetraethylammonium tetrafluoroborate In acetonitrile at 50℃; Electrolysis; Inert atmosphere;
	With chlorine at 0℃;

Reference： [1]Dong, Xichang; Roeckl, Johannes L.; Waldvogel, Siegfried R.; Morandi, Bill [Science, 2021, vol. 371, # 6528]
[2]Current Patent Assignee: SANOFI - DE531336, 1929, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 141][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 141]

4
[ 98-88-4 ]
[ 75-07-0 ]
[ 769-78-8 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: benzoyl chloride With triethylamine In acetonitrile at 20℃; Inert atmosphere; Sealed tube; Stage #2: acetaldehyde In acetonitrile at 40 - 50℃; for 24h; Cooling with ice; Inert atmosphere; Sealed tube;	General procedure for compounds 6a-k General procedure: All used glassware was dried and flushed with argon. A 20mL sealed glass vial wascharged with distilled acyl chloride (2 mmol), dried Et3N (10 mmol for 6a-h/20 mmolfor 6i-j/30 mmol for 6k) and stirred in 5mL dry acetonitrile at room temperature underargon. Afterwards the reaction mixture was cooled with an ice bath and dried acetaldehyde(4 mmol for 6a-h/8 mmol for 6i-j/12 mmol for 6k) was dropped slowly to thismixture. The solution was heated to 40-50 °C and stirred for 24 h, while it turnedorange brown. The reaction progress was monitored via TLC, whereas butanol was usedto react with the residual acid chloride for monitoring the conversion. Furthermore, themixture was diluted in 20mL ethyl acetate, triethylamine was neutralized with sat.NH4Cl (220 mL), washed with and water (240 mL). Before evaporating the solvent,the organic layer was firstly dried with brine (240 mL) and then over Na2SO4. Theorganic phase was filtered and concentrated under reduced pressure. For further purification,the brownish liquid was cleaned via column chromatography. Colorless liquid. Yield 0.23 g (79%). 1H-NMR (400 MHz, CDCl3): d (ppm) 8.08 (2 H,d, J8.0 Hz, o-aromatic), 7.60-7.35 (4 H, m, m-, p-aromatic, CH2CH), 5.05 (1 H, dd,J13.9, 1.5 Hz, trans-CH2), 4.68 (1 H, dd, J6.3, 1.5 Hz, cis-CH2). 13C-NMR(50 MHz, DMSO) d (ppm) 163.52 (CO), 141.40 (CH2CH), 133.55 (aromatic),129.94 (aromatic), 128.90 (aromatic), 128.49 (aromatic), 98.13 (CH2).
	With pyridine
	With triethylamine

Reference： [1]Hofecker, Andreas; Knaack, Patrick; Liska, Robert; Markovic, Marica; Ovsianikov, Aleksandr; Steinbauer, Patrick [Synthetic Communications, 2020, vol. 50, # 23, p. 3629 - 3641]
[2]Jakubowitsch et al. [Zhurnal Obshchei Khimii, 1958, vol. 28, p. 1930,1934; engl. Ausg. S. 1971, 1974] Sladkow; Petrow [Zhurnal Obshchei Khimii, 1954, vol. 24, p. 450,452;engl.Ausg.S.459,460]
[3]Jakubowitsch et al. [Zhurnal Obshchei Khimii, 1958, vol. 28, p. 1930,1934; engl. Ausg. S. 1971, 1974] Sladkow; Petrow [Zhurnal Obshchei Khimii, 1954, vol. 24, p. 450,452;engl.Ausg.S.459,460]

5
[ 108-05-4 ]
[ 65-85-0 ]
[ 769-78-8 ]

Yield	Reaction Conditions	Operation in experiment
85.7%	With 5%-palladium/activated carbon at 80℃; for 10h; Green chemistry;	Transesterification reaction General procedure: A 250-mL four-neck round bottom flask equipped with a reflux condenser and a magnetic stirrer was used as the reactor for the transesterification of vinyl acetate with benzoic acid. The weighed amounts of benzoic acid, vinyl acetate and Pd/C catalyst (SBET = 519 m2/g) were added into the flask and heated in a water bath. The synthesis conditions such as reaction temperature, reaction time, catalyst dosage and benzoic acid/vinyl acetate molar ratio were investigated. After the reaction finished, the temperature of the mixture of the products and unreacted reactants decreased slowly to the room temperature, then ethanol was added into the reaction mixture to dissolve the organic compounds absorbed on the surface of the catalyst. The Pd/C catalyst was separated by filtration and reused after processed in the regenerated experiment. At last, a suitable amount of water was added into the mixture, and two phases were obtained. The upper phase consisted of the unreacted vinyl acetate and vinyl benzoate, and the aqueous phase consisted of acetic acid, ethanol and water. The vinyl benzoate product was separated from the upper layer by distillation. The yield of the product (Y, %) was calculated by Y (%) = WP/WAll × 100, where WP and WAll are the mass of product and the mass of benzoic acid, respectively. The reaction formula for the synthesis of vinyl benzoate is shown in Scheme 1.
82%	With Hg⁽²⁺⁾ adsorbed on UiO-66 bearing sulfhydryl groups at 80℃; for 4h;
91 % Turnov.	With anhydrous Sodium acetate In toluene at 100℃; for 15h;

96 % Chromat.	With silver(I) acetate at 50℃; for 52h;
	at 100℃; for 6h;	6 Examples 4-7; Effect on Transvinylation Reaction Using Catalyst Prepared with Bi-Dentate LigandA catalyst was prepared by using 1,10-phenanthroline as bi-dentate ligand. The catalyst prepared was a diacetato-palladium (II)-1,10-phenanthroline complex. The catalyst was isolated in solid form, dried and used in the reaction.A V-2-EH run was performed with a palladium concentration of 626 ppm based on the mass of 2-EHA in a batch system. After six hours running at 100° C., the conversion achieved was 84.26%. A VB run was also performed with a palladium concentration of 626 ppm based on the mass of BA in a batch system. After six hours running at 100° C., the conversion achieved was 75.56 wt %. In both runs, vinyl acetate was provided in a molar vinyl acetate:carboxylic acid ratio of 4:1. The catalyst performance for each run was at par with the catalyst prepared by using a bi-dentate bipyridyl ligand.
85 %Chromat.	With rhodium(III) chloride trihydrate; anhydrous sodium formate at 80℃; for 24h;	Preparation of vinyl benzoate (2a) In a screw tube, 0.5 mmol benzoic acid, 0.1 mmol formate sodium and 0.2 mol% RhCl3·3H2O were added. After adding of 2 mL vinyl acetate into the screw tube, the reaction system was heated to 80 oC with an oil bath for 24 h. The whole reaction proceeded without the protection of inert gases. After 24 hours’ reaction, wash the mixture of product by sodium bicarbonate aqueous solution to remove the residual benzoic acids and extract the vinylation product by ethyl acetate. Then purify the product by TLC.
	With sulfuric acid; mercury (II) acetate at 78℃;

Reference： [1]Gao, Jun; Guan, Dongrui; Xu, Dongmei; Zhao, Liwen; Zhang, Lianzheng; Li, Min [Bulletin of the Chemical Society of Ethiopia, 2018, vol. 32, # 2, p. 351 - 359]
[2]Guo, Ying; Li, Hong; Sun, Hong-Bin; Wang, Yiming; Xie, Nianyi; Zhang, Gang; Zhang, Xinyue; Zheng, Jianwei; Zhu, Xu [Dalton Transactions, 2022, vol. 51, # 10, p. 4043 - 4051]
[3]Nakagawa, Hideto; Okimoto, Yoshio; Sakaguchi, Satoshi; Ishii, Yasutaka [Tetrahedron Letters, 2003, vol. 44, # 1, p. 103 - 106]
[4]Nakamura, Aki; Tokunaga, Makoto [Tetrahedron Letters, 2008, vol. 49, # 23, p. 3729 - 3732]
[5]Current Patent Assignee: CELANESE CORP - US2011/275852, 2011, A1 Location in patent: Page/Page column 8-9
[6]Jiang, Ruihang; Chen, Zhangpei; Zhan, Kun; Liu, Lei; Zhou, Junjie; Ai, Yongjian; Li, Shuang; Bao, Hongjie; Hu, Ze'nan; Qi, Li; Wang, Jingting; Sun, Hong-bin [Tetrahedron Letters, 2018, vol. 59, # 34, p. 3279 - 3282]
[7]Current Patent Assignee: Carbide & Carbon Chem.Corp. - US2299862, 1939, A Current Patent Assignee: Wacker,A. - US2245131, 1940, A Current Patent Assignee: WACKER CHEMIE AG - DE753039, 1939, C [DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.]

6
[ 65-85-0 ]
[ 74-86-2 ]
[ 769-78-8 ]

Yield	Reaction Conditions	Operation in experiment
55%	In benzoic acid, butyl ester at 180℃; for 4h; Inert atmosphere;	3 Example 3; Example 1 was substantially repeated in several runs using the following conditions. The reaction temperature was maintained at the appropriate temperature; at least one run was operated at each of the following temperatures:1200C, 1400C, 16O0C, 1700C and 1800C. Butyl benzoate was used as a solvent.The amount of benzoic acid used was 100 milligrams in combination with 500 ppm of para-benzoquinone and weight of the catalyst was kept similar so as to result in same metal loading level in all cases based on 50 mg of 0.5% platinum.All catalysts were dried at 500C in air for 16 hours prior to use. The observed results of TON and yield of VB are summarized in Table 2.
99 %Chromat.	In toluene at 140℃; for 6h;	1 Example 1; A mixture of 36.0 g of benzoic acid (295 mmol), 0.25 g of Re2(CO)10 (0.38 mmol) and 78.0 g of toluene were subjected to vinylation at 140° C., a nitrogen pressure of 2 bar and an acetylene pressure of 18 bar for 6 h. The yield determined by GC analysis was 99%.
	In benzoic acid, butyl ester at 140℃; for 4h; Inert atmosphere;	9 Example 9; Example 1 was substantially repeated in several runs using the following conditions. The reaction temperature was maintained at 1400C in all runs. Butyl benzoate was used as a solvent. The amount of benzoic acid used was 360 milligrams in combination with 500 ppm of para-benzoquinone. Appropriate amount of rhenium homogeneous catalyst was used to attain three different levels of molar BA/metal ratios of 385, 1 150 and 3800. Various ligands were also used with each of the rhenium metal complex as summarized in Table 8 with these varied molar BA/metal ratio. Also summarized in Table 8 are the TONs, conversion and selectivity to VB.

With mercury salt

Reference： [1]Current Patent Assignee: CELANESE CORP - WO2010/129029, 2010, A2 Location in patent: Page/Page column 33-34
[2]Current Patent Assignee: BASF SE - US2008/308765, 2008, A1 Location in patent: Page/Page column 5
[3]Current Patent Assignee: CELANESE CORP - WO2010/129030, 2010, A2 Location in patent: Page/Page column 40-41
[4]Current Patent Assignee: RAPID; RAPID PARIS FR; RAPID (unclear) - DE271381, 1988, T1 [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 11, p. 54][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 11, p. 54] Current Patent Assignee: Chem.Fabr.Griesheim-Elektron - DE313696, 1800, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 13, p. 104][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 13, p. 104]

7
[ 769-78-8 ]
[ 79831-76-8 ]
[ 130446-84-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	In pyridine at 45℃;

Reference： [1]Delinck, Deborah L.; Margolin, Alexey L. [Tetrahedron Letters, 1990, vol. 31, # 22, p. 3093 - 3096]

8
[ 769-78-8 ]
[ 86-74-8 ]
[ 19264-68-7 ]

Yield	Reaction Conditions	Operation in experiment
37%	With potassium hydroxide In acetone at 30℃; for 0.5h;

Reference： [1]Shekhirev, Yu. P.; Lopatinskii, V. P.; Sutyagin, V. M.; Tuzovskaya, S. A. [Chemistry of Heterocyclic Compounds, 1983, vol. 19, # 11, p. 1192 - 1197][Khimiya Geterotsiklicheskikh Soedinenii, 1983, # 11, p. 1504 - 1509]

9
[ 769-78-8 ]
[ 13265-84-4 ]
[ 58871-05-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With Lipase from Candida cylindracea (Lipase AY-20) In tetrahydrofuran for 6h; Ambient temperature;
	In tetrahydrofuran; ethyl acetate	17 17. 17. Preparation of 6-O-benzoylglucal 1.0 g (6.85 mmol) of glucal is taken up in 1.5-2.0 ml of tetrahydrofuran and 3-5 ml of vinyl benzoate and stirred with 1 g of lipase from Candida cylindracea (Amano AY-20) at room temperature for 6 h. Filtering off the enzyme, concentration of the solution in vacuo, taking up the residue in ethyl acetate and extracting it with aqueous NaHCO3 solution, and subsequent chromatography on silica gel (ethyl acetate/hexane 1:1) result in 1.20 g (70%) of the desired 6-O-benzoylglucal.

Reference： [1]Holla, E. Wolfgang [Angewandte Chemie, 1989, vol. 101, # 2, p. 222 - 223]
[2]Current Patent Assignee: SANOFI - US5496930, 1996, A

10
[ 67-56-1 ]
[ 201230-82-2 ]
[ 769-78-8 ]
[ 93-58-3 ]
[ 58653-96-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With hydrogenchloride; triphenylphosphine In benzene at 125℃; for 48h; Yields of byproduct given;

Reference： [1]Lee, Chul Woo; Alper, Howard [Journal of Organic Chemistry, 1995, vol. 60, # 1, p. 250 - 252]

11
[ 111-87-5 ]
[ 769-78-8 ]
[ 94-50-8 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 3088 - 3092
[2]Journal of Organic Chemistry,1998,vol. 63,p. 2420 - 2421
[3]Tetrahedron,1999,vol. 55,p. 2899 - 2910

12
[ 201230-82-2 ]
[ 769-78-8 ]
[ 99058-97-6 ]
[ 108552-81-4 ]
[ 78871-04-2 ]

Yield	Reaction Conditions	Operation in experiment
9%	With acetylacetonatodicarbonylrhodium(l); hydrogen; (R,S)-binaphos In benzene at 60℃; for 71h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
76 % ee	With dicarbonylacetylacetonato rhodium (I); C₅₆H₈₀O₉P₂; hydrogen; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In tetrahydrofuran; toluene at 40℃; for 18h; Inert atmosphere; Autoclave;
9 % ee	With C₅₆H₈₀O₉P₂; hydrogen In tetrahydrofuran; toluene at 40℃; for 18h; Inert atmosphere; Autoclave;

Reference： [1]Nozaki, Kyoko; Sakai, Nozomu; Nanno, Tetsuo; Higashijima, Takanori; Mano, Satoshi; Horiuchi, Toshihide; Takaya, Hidemasa [Journal of the American Chemical Society, 1997, vol. 119, # 19, p. 4413 - 4423]
[2]Rovira, Laura; Vaquero, Mónica; Vidal-Ferran, Anton [Journal of Organic Chemistry, 2015, vol. 80, # 20, p. 10397 - 10403]
[3]Rovira, Laura; Vaquero, Mónica; Vidal-Ferran, Anton [Journal of Organic Chemistry, 2015, vol. 80, # 20, p. 10397 - 10403]

13
[ 75-11-6 ]
[ 769-78-8 ]
cyclopropyl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: diiodomethane With diethylzinc; trifluoroacetic acid In hexane; dichloromethane at 0℃; for 0.333333h; Stage #2: vinyl benzoate In hexane; dichloromethane at 20℃; for 0.5h;
90%	Stage #1: diiodomethane With diethylzinc; trifluoroacetic acid In hexane; dichloromethane for 0.333333h; cooling; Stage #2: vinyl benzoate In hexane; dichloromethane at 20℃; for 2.5h;
	With diethylzinc; trifluoroacetic acid 1.) CH₂Cl₂, hexane, 20 min; 2.) CH₂Cl₂, 20 deg C, 150 min; Yield given. Multistep reaction;

Reference： [1]Kim, Jinwoo; Chang, Sukbok [Angewandte Chemie - International Edition, 2014, vol. 53, # 8, p. 2203 - 2207][Angew. Chem., 2014, vol. 126, # 8, p. 2235 - 2239,5]
[2]Lorenz, Jon C.; Long, Jiang; Yang, Zhiqiang; Xue, Song; Xie, Yinong; Shi, Yian [Journal of Organic Chemistry, 2004, vol. 69, # 2, p. 327 - 334]
[3]Yang, Zhiqiang; Lorenz, Jon C.; Shi, Yian [Tetrahedron Letters, 1998, vol. 39, # 47, p. 8621 - 8624]

14
[ 769-78-8 ]
[ 100-51-6 ]
[ 120-51-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With P(MeNCH₂CH₂)3N In tetrahydrofuran for 5.5h; Ambient temperature;
94%	With hexamethyltriamido-N-benzylimidophosphate In tetrahydrofuran at 20℃; for 14.5h;
93%	With N,N'-bismesityl-imidazol-2-ylidene In tetrahydrofuran at 20℃; for 0.0833333h;

92%	With diethylzinc In hexane; toluene at 20℃; for 5h;
87%	With 1,2,4-Triazole; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃;
83%	With C₃₀H₄₂N₂; potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 2h; Molecular sieve;
76%	With TBA₇[γ-HGeW₁₀O₃₆] In acetonitrile at 39.84℃; for 0.0166667h;

Reference： [1]Ilankumaran, Palanichamy; Verkade [Journal of Organic Chemistry, 1999, vol. 64, # 9, p. 3086 - 3089]
[2]Ilankumaran, Palanichamy; Verkade, John G. [Journal of Organic Chemistry, 1999, vol. 64, # 25, p. 9063 - 9066]
[3]Grasa, Gabriela A.; Gueveli, Tatyana; Singh, Rohit; Nolan, Steven P. [Journal of Organic Chemistry, 2003, vol. 68, # 7, p. 2812 - 2819]
[4]Mino, Takashi; Hasegawa, Tae; Shirae, Yoshiaki; Sakamoto, Masami; Fujita, Tsutomu [Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4389 - 4396]
[5]Steemers, Luuk; Wijsman, Linda; van Maarseveen, Jan H. [Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4241 - 4245]
[6]Blümel, Marcus; Noy, Janina-Miriam; Enders, Dieter; Stenzel, Martina H.; Nguyen, Thanh V. [Organic Letters, 2016, vol. 18, # 9, p. 2208 - 2211]
[7]Sugahara, Kosei; Satake, Naoto; Kamata, Keigo; Nakajima, Takahito; Mizuno, Noritaka [Angewandte Chemie - International Edition, 2014, vol. 53, # 48, p. 13248 - 13252][Angew. Chem., 2014, vol. 126, # 48, p. 13464 - 13468,5]

15
[ 769-78-8 ]
n-C₅H₁₁CCH*Co₂(CO)6 [ No CAS ]
[ 25564-22-1 ]

Reference： [1]Chemical Communications,1999,p. 2171 - 2172

16
[ 769-78-8 ]
[ 68882-71-3 ]

Yield	Reaction Conditions	Operation in experiment
33%	With 4-methylmorpholine N-oxide In dichloromethane at 20℃;

Reference： [1]Kerr, William J.; McLaughlin, Mark; Pauson, Peter L.; Robertson, Sarah M. [Chemical Communications, 1999, # 21, p. 2171 - 2172]

17
[ 769-78-8 ]
[ 52418-94-7 ]

Yield	Reaction Conditions	Operation in experiment
61%	With 4-methylmorpholine N-oxide In dichloromethane at 20℃;

Reference： [1]Kerr, William J.; McLaughlin, Mark; Pauson, Peter L.; Robertson, Sarah M. [Chemical Communications, 1999, # 21, p. 2171 - 2172]

18
[ 769-78-8 ]
[ 39545-99-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 4-methylmorpholine N-oxide In dichloromethane at 20℃;

Reference： [1]Kerr, William J.; McLaughlin, Mark; Pauson, Peter L.; Robertson, Sarah M. [Chemical Communications, 1999, # 21, p. 2171 - 2172]

19
[ 769-78-8 ]
[ 173596-03-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 4-methylmorpholine N-oxide In dichloromethane at 20℃;

Reference： [1]Kerr, William J.; McLaughlin, Mark; Pauson, Peter L.; Robertson, Sarah M. [Chemical Communications, 1999, # 21, p. 2171 - 2172]

20
[ 769-78-8 ]
[ 256648-66-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 4-methylmorpholine N-oxide In dichloromethane at 20℃;

Reference： [1]Kerr, William J.; McLaughlin, Mark; Pauson, Peter L.; Robertson, Sarah M. [Chemical Communications, 1999, # 21, p. 2171 - 2172]

21
[ 769-78-8 ]
2-{2,2-dimethyl-3-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-cyclopropyl}-cyclopent-2-enone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With 4-methylmorpholine N-oxide In dichloromethane at 20℃;

Reference： [1]Kerr, William J.; McLaughlin, Mark; Pauson, Peter L.; Robertson, Sarah M. [Chemical Communications, 1999, # 21, p. 2171 - 2172]

22
[ 769-78-8 ]
[ 65-85-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With water In isopropyl alcohol at 60℃; for 18h;
76%	With hydrogen In neat (no solvent) at 220℃; for 22h;
	With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; esterase from Streptomyces diastatochromogenes In water at 25℃;

	With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; esterase from Pseudomonas fluorescens In water at 25℃;
	With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Ophiostoma piliferum In water at 25℃;
	With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Bacillus thermocatenulanatus In water at 40℃;
76 %Spectr.	With hydrogen In neat (no solvent) at 220℃; for 22h; Sealed tube; Glovebox;	Hydrogenolysis of vinyl benzoate Exactly 0.1050 g of vinyl benzoate (dried over CaLh) and 0.0420 g of C/M0O2 (dried under vacuum at 225 °C for 24 h) in a 50: 1 ester group to Mo mole ratio were charged in a 16 x 150 mm reaction tube inside a glove box and sealed with a septum. The septum was then pierced with a needle connected to a gas delivery balloon. The tube and gas delivery balloon were carefully purged with the Lh five times, charged with Lh, and then heated without stirring at 220 °C for 22 h. After the reaction was complete, 2 mL of CD2CI2 containing 0.0371 g of mesitylene was added and 0.5 mL of the reaction mixture was charged in the NMR tube. Product 2 was obtained in 76% yield.

Reference： [1]Aoyama, Hiroshi; Tokunaga, Makoto; Hiraiwa, Shin-Ichiro; Shirogane, Yuki; Obora, Yasushi; Tsuji, Yasushi [Organic Letters, 2004, vol. 6, # 4, p. 509 - 512]
[2]Gao, Yanshan; Kratish, Yosi; Li, Jiaqi; Liu, Shanfu; Marks, Tobin J. [Angewandte Chemie - International Edition, 2020, vol. 59, # 45, p. 19857 - 19861][Angew. Chem., 2020, vol. 132, # 45, p. 20029 - 20033,5]
[3]Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D. [Tetrahedron Asymmetry, 2001, vol. 12, # 4, p. 545 - 556]
[4]Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D. [Tetrahedron Asymmetry, 2001, vol. 12, # 4, p. 545 - 556]
[5]Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D. [Tetrahedron Asymmetry, 2001, vol. 12, # 4, p. 545 - 556]
[6]Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D. [Tetrahedron Asymmetry, 2001, vol. 12, # 4, p. 545 - 556]
[7]Current Patent Assignee: NORTHWESTERN UNIVERSITY (ILLINOIS) - WO2021/211423, 2021, A1 Location in patent: Paragraph 0012; 0060-0061

23
[ 769-78-8 ]
[ 107-19-7 ]
[ 68882-71-3 ]

Yield	Reaction Conditions	Operation in experiment
33%	Stage #1: propargyl alcohol With dicobalt octacarbonyl Stage #2: vinyl benzoate With 4-methylmorpholine N-oxide In dichloromethane at 25℃; for 18h;

Reference： [1]Kerr, William J.; McLaughlin, Mark; Pauson, Peter L.; Robertson, Sarah M. [Journal of Organometallic Chemistry, 2001, vol. 630, # 1, p. 104 - 117]

24
[ 100-42-5 ]
[ 769-78-8 ]
[ 530-48-3 ]
[ 645-49-8 ]

Yield	Reaction Conditions	Operation in experiment
	With isoquinoline; lithium chloride In various solvent(s) at 160℃; for 16h;

Reference： [1]Goossen, Lukas J.; Paetzold [Angewandte Chemie - International Edition, 2002, vol. 41, # 7, p. 1237 - 1241]

25
[ 2163-42-0 ]
[ 769-78-8 ]
[ 141978-59-8 ]
[ 141978-58-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-di-(S)-((((4-Ph-Ph)2C(OH))C₄H₇N)CH₂)-4-MeC₆H₂OH In toluene at -20℃; for 20h; Title compound not separated from byproducts.;
	With (S,S)-2,6-bis{2-[hydroxy(biphenyl-4-yl)methyl]pyrrolidin-1-ylmethyl}-4-methylphenol; diethylzinc In toluene at -20℃; for 20h; Inert atmosphere; optical yield given as %ee;

Reference： [1]Trost, Barry M.; Mino, Takashi [Journal of the American Chemical Society, 2003, vol. 125, # 9, p. 2410 - 2411]
[2]Location in patent: scheme or table Trost, Barry M.; Malhotra, Sushant; Mino, Takashi; Rajapaksa, Naomi S. [Chemistry - A European Journal, 2008, vol. 14, # 25, p. 7648 - 7657]

26
[ 6725-55-9 ]
[ 769-78-8 ]
(+)-3-benzyloxy-2-(4'-biphenyl)-1-propanol [ No CAS ]
Benzoic acid (S)-2-biphenyl-4-yl-3-hydroxy-propyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-di-(S)-((((4-Ph-Ph)2C(OH))C₄H₇N)CH₂)-4-MeC₆H₂OH In toluene at -15℃; for 18h; Title compound not separated from byproducts.;
	With (S,S)-2,6-bis{2-[hydroxy(biphenyl-4-yl)methyl]pyrrolidin-1-ylmethyl}-4-methylphenol; diethylzinc In toluene at -15℃; Inert atmosphere; optical yield given as %ee;

Reference： [1]Trost, Barry M.; Mino, Takashi [Journal of the American Chemical Society, 2003, vol. 125, # 9, p. 2410 - 2411]
[2]Location in patent: scheme or table Trost, Barry M.; Malhotra, Sushant; Mino, Takashi; Rajapaksa, Naomi S. [Chemistry - A European Journal, 2008, vol. 14, # 25, p. 7648 - 7657]

27
[ 15753-50-1 ]
[ 769-78-8 ]
Benzoic acid (1S,2R)-2-hydroxymethyl-cyclohexylmethyl ester [ No CAS ]
(+)-cis-2-(benzyloxymethyl)cyclohexanemethanol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 2410 - 2411

28
[ 769-78-8 ]
[ 4424-32-2 ]
(-)-3-benzyloxy-2-(4'-tolyl)-1-propanol [ No CAS ]
benzoic acid 3-hydroxy-2-<i>p</i>-tolyl-propyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-di-(S)-((((4-Ph-Ph)2C(OH))C₄H₇N)CH₂)-4-MeC₆H₂OH In toluene at -15℃; for 24h; Title compound not separated from byproducts.;

Reference： [1]Trost, Barry M.; Mino, Takashi [Journal of the American Chemical Society, 2003, vol. 125, # 9, p. 2410 - 2411]

29
[ 201230-82-2 ]
[ 769-78-8 ]
1-oxopropan-2-yl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With di(rhodium)tetracarbonyl dichloride; (diphenylphosphinoyl)(phenyl)methanol; hydrogen In chloroform at 50℃; for 20h;
30 % Chromat.	With hydrogen In dichloromethane at 50℃; for 16h;
	With hydrogen In dichloromethane at 25℃; for 22h;

	With hydrogen In toluene at 100℃; Autoclave; regioselective reaction;
	With triphenyl phosphite; acetylacetonatodicarbonylrhodium(l); hydrogen In toluene at 60℃; for 16h; Inert atmosphere; Autoclave; regioselective reaction;
	With hydrogen In dichloromethane at 80℃; for 16h; Autoclave; regioselective reaction;	3.9. General procedure for the hydroformylation reaction General procedure: 5 mmol of the suitable substrate were mixed with the appropriatecatalyst containing 0.01 mmol rhodium in 2 mL solvent. Theresulting mixture was placed in 45 mL glass-lined autoclave. Theautoclave was sealed, purged three times with carbon monoxideand pressurized to 1000 psi with a 1:1 mixture of carbon monoxideand hydrogen. The autoclave was placed in an oil bath preset to thedesired temperature. After 16 h, the autoclave was cooled to roomtemperature and the gases were released. The separation of thecatalyst was performed by applying an external magnetic field, inthe case of using catalysts 3a and 3b, or by evaporation of thesolvent and extracting the products with ether in the case of usingcatalysts 2a and 2b. The resulted products were analysed by 1HNMR and GC.

Reference： [1]Clark, Helen J.; Wang, Ruiping; Alper, Howard [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 6224 - 6225]
[2]Abu-Reziq, Raed; Alper, Howard; Wang, Dashan; Post, Michael L. [Journal of the American Chemical Society, 2006, vol. 128, # 15, p. 5279 - 5282]
[3]Location in patent: scheme or table Vasylyev, Maksym; Alper, Howard [Synthesis, 2010, # 17, p. 2893 - 2900]
[4]Location in patent: experimental part Sudheesh; Chaturvedi, Amit K.; Shukla, Ram S. [Applied Catalysis A: General, 2011, vol. 409-410, p. 99 - 105]
[5]Holthusen, Katharina; Leitner, Walter; Franciò, Giancarlo [Journal of Organic Chemistry, 2016, vol. 81, # 11, p. 4823 - 4828]
[6]Omar, Suheir; Dutta, Bishnu; Natour, Suzana; Abu-Reziq, Raed [Journal of Organometallic Chemistry, 2016, vol. 818, p. 48 - 57]

30
[ 769-78-8 ]
[ 131605-38-4 ]
(-)-3-benzyloxy-2-(3'-thiophene)-1-propanol [ No CAS ]
Benzoic acid (S)-3-hydroxy-2-thiophen-3-yl-propyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-di-(S)-((((4-Ph-Ph)2C(OH))C₄H₇N)CH₂)-4-MeC₆H₂OH In toluene at -15℃; for 20h; Title compound not separated from byproducts.;
	With (S,S)-2,6-bis{2-[hydroxy(biphenyl-4-yl)methyl]pyrrolidin-1-ylmethyl}-4-methylphenol; diethylzinc In toluene at -15℃; Inert atmosphere; optical yield given as %ee;

Reference： [1]Trost, Barry M.; Mino, Takashi [Journal of the American Chemical Society, 2003, vol. 125, # 9, p. 2410 - 2411]
[2]Location in patent: scheme or table Trost, Barry M.; Malhotra, Sushant; Mino, Takashi; Rajapaksa, Naomi S. [Chemistry - A European Journal, 2008, vol. 14, # 25, p. 7648 - 7657]

31
[ 769-78-8 ]
[ 131605-37-3 ]
(-)-3-benzyloxy-2-(2'-thiophene)-1-propanol [ No CAS ]
Benzoic acid (S)-3-hydroxy-2-thiophen-2-yl-propyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-di-(S)-((((4-Ph-Ph)2C(OH))C₄H₇N)CH₂)-4-MeC₆H₂OH In toluene at -15℃; for 20h; Title compound not separated from byproducts.;
	With (S,S)-2,6-bis{2-[hydroxy(biphenyl-4-yl)methyl]pyrrolidin-1-ylmethyl}-4-methylphenol; diethylzinc In toluene at -15℃; Inert atmosphere; optical yield given as %ee;

Reference： [1]Trost, Barry M.; Mino, Takashi [Journal of the American Chemical Society, 2003, vol. 125, # 9, p. 2410 - 2411]
[2]Location in patent: scheme or table Trost, Barry M.; Malhotra, Sushant; Mino, Takashi; Rajapaksa, Naomi S. [Chemistry - A European Journal, 2008, vol. 14, # 25, p. 7648 - 7657]

32
[ 769-78-8 ]
[ 122098-61-7 ]
(+)-3-benzyloxy-2-(4'-chlorophenyl)-1-propanol [ No CAS ]
Benzoic acid (S)-2-(4-chloro-phenyl)-3-hydroxy-propyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-di-(S)-((((4-Ph-Ph)2C(OH))C₄H₇N)CH₂)-4-MeC₆H₂OH In toluene at -15℃; for 18h; Title compound not separated from byproducts.;

Reference： [1]Trost, Barry M.; Mino, Takashi [Journal of the American Chemical Society, 2003, vol. 125, # 9, p. 2410 - 2411]

33
[ 769-78-8 ]
[ 82520-34-1 ]
(-)-3-benzyloxy-2-(4'-methoxyphenyl)-1-propanol [ No CAS ]
Benzoic acid (S)-3-hydroxy-2-(4-methoxy-phenyl)-propyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-di-(S)-((((4-Ph-Ph)2C(OH))C₄H₇N)CH₂)-4-MeC₆H₂OH In toluene at -15℃; for 24h; Title compound not separated from byproducts.;

Reference： [1]Trost, Barry M.; Mino, Takashi [Journal of the American Chemical Society, 2003, vol. 125, # 9, p. 2410 - 2411]

34
[ 769-78-8 ]
[ 130210-24-1 ]
(-)-3-benzyloxy-2-(2'-naphthyl)-1-propanol [ No CAS ]
Benzoic acid (S)-3-hydroxy-2-naphthalen-2-yl-propyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-di-(S)-((((4-Ph-Ph)2C(OH))C₄H₇N)CH₂)-4-MeC₆H₂OH In toluene at -15℃; for 18h; Title compound not separated from byproducts.;

Reference： [1]Trost, Barry M.; Mino, Takashi [Journal of the American Chemical Society, 2003, vol. 125, # 9, p. 2410 - 2411]

35
[ 106-24-1 ]
[ 769-78-8 ]
[ 94-48-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N,N'-bismesityl-imidazol-2-ylidene In tetrahydrofuran at 20℃; for 1h;

Reference： [1]Grasa, Gabriela A.; Gueveli, Tatyana; Singh, Rohit; Nolan, Steven P. [Journal of Organic Chemistry, 2003, vol. 68, # 7, p. 2812 - 2819]

36
[ 769-78-8 ]
[ 4407-36-7 ]
[ 50555-04-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With N,N'-biscyclohexyl-imidazol-2-ylidene In tetrahydrofuran at 20℃; for 0.5h;
92%	With diethylzinc In hexane; toluene at 20℃; for 4h;

Reference： [1]Grasa, Gabriela A.; Gueveli, Tatyana; Singh, Rohit; Nolan, Steven P. [Journal of Organic Chemistry, 2003, vol. 68, # 7, p. 2812 - 2819]
[2]Mino, Takashi; Hasegawa, Tae; Shirae, Yoshiaki; Sakamoto, Masami; Fujita, Tsutomu [Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4389 - 4396]

37
[ 769-78-8 ]
[ 191916-39-9 ]
methyl 4-O-benzoylquinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With Candida antarctica Lipase A; 4 A molecular sieve In various solvent(s) at 40℃; for 9h;

Reference： [1]Armesto, Nuria; Ferrero, Miguel; Fernandez, Susana; Gotor, Vicente [Journal of Organic Chemistry, 2003, vol. 68, # 14, p. 5784 - 5787]

38
[ 68892-42-2 ]
[ 769-78-8 ]
[ 104769-15-5 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 1709 - 1712
[2]European Journal of Organic Chemistry,2010,p. 1736 - 1744

39
[ 769-78-8 ]
but-3-yn-2-yl benzoate [ No CAS ]
benzoic acid 4-benzyloxy-1-methyl-2-methylene-but-3-enyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With ethene In benzene at 20℃; for 20h;

Reference： [1]Giessert, Anthony J.; Brazis, Nicholas J.; Diver, Steven T. [Organic Letters, 2003, vol. 5, # 21, p. 3819 - 3822]

40
[ 769-78-8 ]
[ 4836-13-9 ]
[ 4803-92-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With Candida antarctica lipase B In tetrahydrofuran at 60℃; for 40h;
92%	With Candida antarctica lipase B In tetrahydrofuran at 60℃; for 68h; Inert atmosphere; Enzymatic reaction; regioselective reaction;

Reference： [1]García, Javier; Fernández, Susana; Ferrero, Miguel; Sanghvi, Yogesh S.; Gotor, Vicente [Tetrahedron Letters, 2004, vol. 45, # 8, p. 1709 - 1712]
[2]Location in patent: experimental part Rodriguez-Perez, Tatiana; Fernandez, Susana; Martinez-Montero, Saul; Gonzalez-Garcia, Tania; Sanghvi, Yogesh S.; Gotor, Vicente; Ferrero, Miguel [European Journal of Organic Chemistry, 2010, # 9, p. 1736 - 1744]

41
[ 769-78-8 ]
[ 4546-72-9 ]
[ 104769-16-6 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 1709 - 1712
[2]European Journal of Organic Chemistry,2010,p. 1736 - 1744

42
[ 769-78-8 ]
[ 50-89-5 ]
5'-benzoylthymidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With Candida antarctica lipase B In tetrahydrofuran at 60℃; for 63h;
93%	With Candida antarctica lipase B In tetrahydrofuran at 60℃; for 116h; Inert atmosphere; Enzymatic reaction; regioselective reaction;

Reference： [1]García, Javier; Fernández, Susana; Ferrero, Miguel; Sanghvi, Yogesh S.; Gotor, Vicente [Tetrahedron Letters, 2004, vol. 45, # 8, p. 1709 - 1712]
[2]Location in patent: experimental part Rodriguez-Perez, Tatiana; Fernandez, Susana; Martinez-Montero, Saul; Gonzalez-Garcia, Tania; Sanghvi, Yogesh S.; Gotor, Vicente; Ferrero, Miguel [European Journal of Organic Chemistry, 2010, # 9, p. 1736 - 1744]

43
[ 769-78-8 ]
[ 172475-95-5 ]
[ 581-47-5 ]

Reference： [1]Chemistry Letters,2005,vol. 34,p. 836 - 837

44
[ 288-32-4 ]
[ 769-78-8 ]
1-(imidazol-1-yl)ethyl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; Inert atmosphere;
84%	With [bmIm]OH at 50℃; for 12h;
26%	With Escherichia coli (EC 3.5.1.81) D-aminoacylase In hexane at 50℃; for 192h;

Reference： [1]Steemers, Luuk; Wijsman, Linda; van Maarseveen, Jan H. [Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4241 - 4245]
[2]Xu, Jian-Ming; Liu, Bo-Kai; Wu, Wei-Bo; Qian, Chao; Wu, Qi; Lin, Xian-Fu [Journal of Organic Chemistry, 2006, vol. 71, # 10, p. 3991 - 3993]
[3]Wu, Wei-Bo; Xu, Jian-Ming; Wu, Qi; Lv, De-Shui; Lin, Xian-Fu [Synlett, 2005, # 16, p. 2433 - 2436]

45
[ 769-78-8 ]
[ 3034-38-6 ]
1-(4-nitro-imidazol-1-yl)-ethyl benzoate [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 1555 - 1558
[2]Journal of Organic Chemistry,2006,vol. 71,p. 3991 - 3993
[3]Advanced Synthesis and Catalysis,2006,vol. 348,p. 487 - 492

46
[ 769-78-8 ]
poly(vinyl benzoate), M_n 1.08E₄ Da, PDI 2.16; monomer(s): vinyl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.3%	With 2,2'-azobis(isobutyronitrile) In toluene at 100℃; for 0.25h;

Reference： [1]Iwasaki, Takeshi; Yoshida, Jun-Ichi [Macromolecules, 2005, vol. 38, # 4, p. 1159 - 1163]

47
[ 769-78-8 ]
poly(vinyl benzoate), M_n 1.04E₄ Da, PDI 2.16; monomer(s): vinyl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58.3%	With 2,2'-azobis(isobutyronitrile) In toluene at 100℃; for 0.25h;

Reference： [1]Iwasaki, Takeshi; Yoshida, Jun-Ichi [Macromolecules, 2005, vol. 38, # 4, p. 1159 - 1163]

48
[ 769-78-8 ]
[ 696-23-1 ]
1-(2-methyl-4-nitro-1H-imidazol-1-yl)ethyl benzoate [ No CAS ]

Reference： [1]Synthesis,2007,p. 1933 - 1938

49
[ 769-78-8 ]
[ 35059-50-8 ]
(1S*,2R*)-2-(tert-butoxycarbonyl)cyclopropyl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With C₆₇H₅₁IrN₂O₂ In tetrahydrofuran at -78℃; for 72.1667h; optical yield given as %ee; enantioselective reaction;

Reference： [1]Location in patent: experimental part Suematsu, Hidehiro; Kanchiku, Shigefumi; Uchida, Tatsuya; Katsuki, Tsutomu [Journal of the American Chemical Society, 2008, vol. 130, # 31, p. 10327 - 10337]

50
[ 2163-42-0 ]
[ 769-78-8 ]
[ 141978-58-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With diethylzinc; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol) In toluene at -20℃; for 24h; Inert atmosphere; optical yield given as %ee;

Reference： [1]Trost, Barry M.; Malhotra, Sushant; Mino, Takashi; Rajapaksa, Naomi S. [Chemistry - A European Journal, 2008, vol. 14, # 25, p. 7648 - 7657]

51
[ 1570-95-2 ]
[ 769-78-8 ]
(S)-3-hydroxy-2-phenylpropyl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With (S,S)-2,6-bis{2-[hydroxy(biphenyl-4-yl)methyl]pyrrolidin-1-ylmethyl}-4-methylphenol; diethylzinc In toluene at -15℃; Inert atmosphere; optical yield given as %ee;

Reference： [1]Location in patent: scheme or table Trost, Barry M.; Malhotra, Sushant; Mino, Takashi; Rajapaksa, Naomi S. [Chemistry - A European Journal, 2008, vol. 14, # 25, p. 7648 - 7657]

52
[ 934008-48-7 ]
[ 769-78-8 ]
2-(1-(benzoyloxy)ethyl)-1,3-bis(2,6-diisopropyl-4-iodo-phenyl)-1H-imidazol-3-ium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: 1,3-bis(4-iodo-2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride With potassium <i>tert</i>-butylate In tetrahydrofuran for 0.166667h; Stage #2: vinyl benzoate In tetrahydrofuran

Reference： [1]Pignataro, Luca; Papalia, Teresa; Slawin, Alexandra M. Z.; Goldup, Stephen M. [Organic Letters, 2009, vol. 11, # 7, p. 1643 - 1646]

53
[ 1158187-83-7 ]
[ 769-78-8 ]
[ 1158187-93-9 ]
2-cyano-2-(pyrrolidine-1-carbonyl)cyclopropyl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: vinyl benzoate With tetrakis[μ-(αS)-α-(1,1-dimethylethyl)-2,3-dihydro-1H-naphtho[1,8-cd]pyridine-2-acetato-κO:.kappaO']dirhodium(II)(Rh-Rh); Trifluoromethanesulfonamide In toluene at -78℃; for 0.25h; Inert atmosphere; Stage #2: 2-oxo-2-(pyrrolidin-1-yl)ethanecarbonimidoyl cyanide In toluene at -78 - 25℃; for 22h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

Reference： [1]Marcoux, David; Azzi, Soula; Charette, Andre B. [Journal of the American Chemical Society, 2009, vol. 131, p. 6970 - 6972]

54
[ 769-78-8 ]
[ 497-76-7 ]
[ 71202-99-8 ]

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2010,vol. 67,p. 41 - 44

55
[ 592-41-6 ]
[ 375-80-4 ]
[ 769-78-8 ]
[ 1208999-63-6 ]

Reference： [1]Bioconjugate Chemistry,2010,vol. 21,p. 360 - 371

56
[ 629-05-0 ]
[ 375-80-4 ]
[ 769-78-8 ]
3,3,4,4,5,5,6,6,7,7,8,8-dodecafluoro-1,10-diiodohexadec-9-enyl benzoate [ No CAS ]
3,3,4,4,5,5,6,6,7,7,8,8-dodecafluoro-1,10-diiodohexadec-9-enyl benzoate [ No CAS ]

Reference： [1]Bioconjugate Chemistry,2010,vol. 21,p. 360 - 371

57
[ 872-05-9 ]
[ 375-80-4 ]
[ 769-78-8 ]
[ 1208999-65-8 ]

Reference： [1]Bioconjugate Chemistry,2010,vol. 21,p. 360 - 371

58
[ 769-78-8 ]
[ 1308660-31-2 ]
[ 1197398-08-5 ]

Yield	Reaction Conditions	Operation in experiment
99.99 % ee	In acetone at 25℃; for 21h; Enzymatic reaction;	21 Example 21; Vinyl Benzoate Reaction 199.0 mg of the compound of Formula 2 was dissolved in a mixed solution of 7.2 mL of vinyl benzoate and 0.8 mL of acetone, 150 mg of the same immobilized enzyme as that prepared in Example 19 was added, and an enzymatic reaction was carried out by stirring using a stirrer (600 rpm) at 25° C. for 21 hours.After the reaction was completed, the reaction mixture was filtered using an Ekicrodisc 25CR so as to remove the immobilized enzyme and then purified by flash silica gel column chromatography (eluent: n-hexane/ethyl acetate), thus giving 18.0 mg of a compound of Formula 3-2 as a colorless solid (optical purity 99.99% e.e.).1H NMR (500 MHz, CDCl3): δ 2.13 (ddd, J=4.5, 16.5 Hz, 1H), 2.40 (ddd, J=3.0, 7.0, 10.0 Hz, 1H), 2.47 (dd, J=6.5 Hz, 1H), 2.59 (dd, J=6.5 Hz 1H), 3.82 (s, 3H), 4.51 (dt, J=6.0 Hz, 1H), 5.53 (dt, J=5.5 Hz 1H), 7.46 (t, J=8.0 Hz, 2H), 7.59 (t, J=8.0 Hz, 1H), 8.04 (d, J=8.5 Hz, 1H), 8.05 (d, J=8.0 Hz, 1H). 13C NMR (125 MHz, CDCl3): δ 35.11 (d, J=10.3 Hz), 38.08 (d, J=11.7 Hz), 42.73 (d, J=9.1 Hz), 52.99, 73.19, 76.25, 128.49, 129.65, 133.35, 165.80, 168.46, 168.67. MS (Shimadzu LCMS-210EV ESI/APCI Dual positive) m/z: [M+Na]+317.0, [α]D24=-11.0 degIn addition, the state of the starting material compound of Formula 2 and formation of the target compound of Formula 3-2 were confirmed by the TLC method and the HPLC method below.(TLC method; TLC plate; silica gel Si60 (Art 1.5715, Merck & Co., Inc.)) Developing solvent; n-hexane/ethyl acetate=10/1 Coloration; anisaldehyde/conc. sulfuric acid/acetic acid=1/2/100 Rf value; compound of Formula 2=0.20, compound of Formula 3-2=0.58 (HPLC method: column CHIRALCEL OJ-RH 4.6 mm ID×150 mm L (Daicel Chemical Industries, Ltd.)) Mobile phase; (methanol:acetonitrile=1:1)/0.1% phosphoric acid aqueous solution=52/48 Flow rate; 0.8 mL/min Temperature; 35° C.Detection; UV 195 nmRetention time; compound of Formula 3-2: 8.1 min

Reference： [1]Current Patent Assignee: TAISHO PHARMACEUTICAL HOLDINGS CO., LTD. - US2011/65934, 2011, A1 Location in patent: Page/Page column 22

59
[ 769-78-8 ]
[ 56-75-7 ]
[ 492-79-5 ]

Yield	Reaction Conditions	Operation in experiment
45%	With immobilised Pseudomonas cepacia lipase PSL-C I; In 1,4-dioxane; at 30℃; for 48h;Inert atmosphere; Enzymatic reaction;	General procedure: To a suspension of (-)-<strong>[56-75-7]chloramphenicol</strong> (1, 100 mg, 0.301 mmol) and the corresponding enzyme (CAL-B or PSL, ratio 1:1 in weight respecting 1) in dry solvent (MeCN or 1,4-dioxane, 2.0 mL), the corresponding vinyl ester 3a-f (5 equiv., 1.505 mmol) was added under nitrogen atmosphere. The reaction was shaken at 20 or 30 C and 250 rpm, and aliquots were regularly analysed by HPLC. The reaction was stopped after complete consumption of the starting material, and then the enzyme was filtered off and washed with EtOAc (3 x 10 mL). Finally the solvent was evaporated under reduced pressure, and the reaction crude purified by flash chromatography on silica gel using mixtures of EtOAc/hexane to afford the desired ester (2'R,3'R)-2a-f.

Reference： [1]Tetrahedron,2011,vol. 67,p. 2858 - 2862

60
[ 123-34-2 ]
[ 769-78-8 ]
[ 1375077-61-4 ]
[ 204070-27-9 ]

Yield	Reaction Conditions	Operation in experiment
	With Muchor miehei lipase In tert-butyl methyl ether at 20℃; for 0.5h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;	4.2. General procedure for lipase-mediated benzoylation and acetylation of 3-allyloxy-propane-1,2-diol 1 General procedure: Substrates (1.0 mmol), VA or VB, (3.0 mmol) and lipase (PCL 80 mg; MML 100 mg; CAL 200 mg) were suspended in 10.0 ml of tBuOMe. The mixture was stirred at rt and the formation of the acetylated or benzoylated compounds was monitored by GC analysis. The reaction was stopped at the reported conversion (see Table 1) by filtration of the enzyme and evaporation of the solvent at reduced pressure. The residue was then purified by chromatography. For time, see Table 1.

Reference： [1]Location in patent: experimental part Casati, Silvana; Santaniello, Enzo; Ciuffreda, Pierangela [Tetrahedron Asymmetry, 2012, vol. 23, # 5, p. 395 - 400]

61
[ 769-78-8 ]
[ 74554-16-8 ]
[ 143381-04-8 ]

Yield	Reaction Conditions	Operation in experiment
48.7%	With Burkholderia cepacia Amano PS lipase In tert-butyl methyl ether at 50℃; for 24h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;	4.3.3. Preparative scale enzymatic acylation of diol 1 General procedure: To a solution of 1 (1 × 10-3 mol) in TBME (20 mL), lipase BCL (3.5 g) and acyl donor (1 × 10-3 mol) were added. The reaction mixture was kept at a constant temperature (50 °C). The reaction progress was monitored by TLC and HPLC. After 24 h, the reaction was quenched by filtration and the filtrate was concentrated under reduced pressure. The crude product was purified by PLC using ethyl acetate as eluent.4.3.3.1. 3-Hydroxy-2-((5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methoxy)propyl acetate 2'Isolated yield: 30%;

Reference： [1]Location in patent: experimental part Kolodziejska, Renata; Gorecki, Marcin; Frelek, Jadwiga; Draminski, Marcin [Tetrahedron Asymmetry, 2012, vol. 23, # 9, p. 683 - 689]

62
[ 201230-82-2 ]
[ 769-78-8 ]
[ 108552-81-4 ]
[ 78871-04-2 ]

Yield	Reaction Conditions	Operation in experiment
71 % ee	With (acetylacetonato)dicarbonylrhodium (l); caesium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; C₇₆H₈₈O₁₂P₂Si₄; hydrogen In tetrahydrofuran; toluene at 40℃; for 18h; Glovebox; Inert atmosphere; Autoclave; enantioselective reaction;
14 % ee	With (acetylacetonato)dicarbonylrhodium (l); C₆₀H₇₂O₉P₂Si₄; hydrogen In tetrahydrofuran; toluene Autoclave;
	With dicarbonyl(acetylacotonato)rhodium(I); (R,R,R)-bisdiazaphospholane; hydrogen In tetrahydrofuran at 60℃; Inert atmosphere; Glovebox;

With dicarbonylacetylacetonato rhodium (I); hydrogen; C₉₆H₉₂N₄O₈Zn; tri(pyridin-3-yl)phosphine In toluene at 25 - 135℃; for 1h; Autoclave; Overall yield = 63 percentSpectr.; Optical yield = 21 percent ee;

Reference： [1]Mon, Ignasi; Jose, D. Amilan; Vidal-Ferran, Anton [Chemistry - A European Journal, 2013, vol. 19, # 8, p. 2720 - 2725]
[2]Vidal-Ferran, Anton; Mon, Ignasi; Bauzá, Antonio; Frontera, Antonio; Rovira, Laura [Chemistry - A European Journal, 2015, vol. 21, # 32, p. 11417 - 11426]
[3]Miles, Kelsey C.; Abrams, M. Leigh; Landis, Clark R.; Stahl, Shannon S. [Organic Letters, 2016, vol. 18, # 15, p. 3590 - 3593]
[4]Jongkind, Lukas J.; Reek, Joost N. H. [Chemistry - An Asian Journal, 2020, vol. 15, # 6, p. 867 - 875]

63
[ 769-78-8 ]
[ 97-30-3 ]
[ 4338-28-7 ]
[ 26927-44-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 76% 2: 13%	With Lipolase 100T In acetonitrile at 20 - 37℃; for 98h; Enzymatic reaction; regioselective reaction;	4. General procedure for enzymatic acylation of Me α-D-Glc_p General procedure: Me α-D-Glcp (1) (1 mmol), vinyl carboxylate (1.5 mmol, 1.5 equiv.) and Lipolase 100T (3 g) were added to 20 mL of acetonitrile at room temperature. The reaction mixtures were stirred at 37°C for several hours (Table 1) and finished by filtration. The filter cake was washed with acetone and combined organic phases were concentrated under reduced pressure. Crude mixtures were purified by silica-gel chromatography (toluene/ethylacetate, 2:1→0:1) to afford first 2,6-di-O-acyl and next 6-O-acyl products.

Reference： [1]Mastihubova, Maria; Mastihuba, Vladimir [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 19, p. 5389 - 5392]

64
dicarbonyl(acetylacotonato)rhodium(I) [ No CAS ]
[ 201230-82-2 ]
[ 769-78-8 ]
1-oxopropan-2-yl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,3-bis[(diphenylphosphino)oxy]-1,3-diphenylpropane; hydrogen In toluene at 90℃; for 6h; Inert atmosphere; regioselective reaction;	2.3 General procedure for catalytic hydroformylation reaction General procedure: In a typical experiment, to a high pressure reactor (autoclave) of 100mL capacity, Rh(acac)(CO)2 (0.001mmol), ligand L1 (0.002mmol), vinyl ester (10mmol) and toluene (15ml) were added. The reactor was then flushed with nitrogen, followed by syngas (1:1 mixture of CO and H2 gas) at room temperature; next, the reaction was pressurized to 4MPa syngas and heated to 90°C at a stirring speed of 600rpm for 6h. After completion of the reaction, the reactor was cooled to room temperature and remaining syngas was carefully released. The reaction mixture was analyzed by gas chromatography (Perkin Elmer, Clarus 400 GC) equipped with capillary column (30m×0.25mm×0.25μm) and a flame ionization detector (FID). For the ease of catalyst weighing, the stock solution of Rh(acac)(CO)2 was prepared in toluene and was used for the reaction. The products obtained are well known in literature and were confirmed by GC-MS analysis (Shimadzu, GCMSQP2010) equipped with Rtx wax capillary column (30m length and 0.25mm diameter).

Reference： [1]Khan, Shoeb R.; Bhanage, Bhalchandra M. [Catalysis Communications, 2014, vol. 46, p. 109 - 112]

65
[ 769-78-8 ]
[ 93-89-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogen; sodium hydroxide In methanol; water at 25℃; for 4h; Autoclave;
98%	With [(COD)Ir(dimethylphenylphosphine)(1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene)](tetrakis(3,5-bis(trifluoromethyl)phenyl)borate); hydrogen In dichloromethane at -78 - 25℃; for 16h; chemoselective reaction;
99 %Spectr.	With hydrogen In water at 20℃; for 6.5h; Autoclave;

Reference： [1]Queffélec, Clémence; Schlindwein, Simon H.; Gudat, Dietrich; Silvestre, Virginie; Rodriguez-Zubiri, Mireia; Fayon, Franck; Bujoli, Bruno; Wang, Qi; Boukherroub, Rabah; Szunerits, Sabine [ChemCatChem, 2017, vol. 9, # 3, p. 432 - 439]
[2]Kerr, William J.; Mudd, Richard J.; Brown, Jack A. [Chemistry - A European Journal, 2016, vol. 22, # 14, p. 4738 - 4742]
[3]Weiss, Ester; Dutta, Bishnu; Schnell, Yafit; Abu-Reziq, Raed [Journal of Materials Chemistry A, 2014, vol. 2, # 11, p. 3971 - 3977]

66
[ 769-78-8 ]
[ 618-36-0 ]
[ 3480-59-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	In neat (no solvent) at 20℃; for 24h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

67
[ 769-78-8 ]
[ 625-30-9 ]
[ 80936-85-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	In neat (no solvent) at 20℃; for 4h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

68
[ 96-15-1 ]
[ 769-78-8 ]
[ 54449-43-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	In neat (no solvent) at 20℃; for 3h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

69
[ 769-78-8 ]
[ 100-46-9 ]
[ 1485-70-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 1,2,4-Triazole; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃;
70%	In neat (no solvent) at 20℃; for 24h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.
	With zirconocene dichloride In toluene at 110℃; for 20h;	2 4.1. General procedure General procedure: Carboxylic ester (5.0 mmol), amine (6.5 mmol), and Cp2ZrCl2 (146.7 mg, 0.5 mmol) were suspended in 1.2 mL of anhydrous toluene. The reaction was stirred at 110°C for 4-20 h. The solvent was then removed under reduced pressure. The crude product was purified on a Biotage Isolera One using a Biotage SNAP Ultra cartridge (12 g or 25 g, 10-60% EtOAc in n-heptane) to isolate the desired amide.

Reference： [1]Steemers, Luuk; Wijsman, Linda; van Maarseveen, Jan H. [Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4241 - 4245]
[2]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]
[3]Lenstra, Danny C.; Nguyen, D. Thao; Mecinović, Jasmin [Tetrahedron, 2015, vol. 71, # 34, p. 5547 - 5553]

70
[ 34967-24-3 ]
[ 769-78-8 ]
[ 20781-29-7 ]

Yield	Reaction Conditions	Operation in experiment
68%	In neat (no solvent) at 20℃; for 24h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

71
[ 769-78-8 ]
[ 72235-53-1 ]
[ 1379160-31-2 ]

Yield	Reaction Conditions	Operation in experiment
55%	In neat (no solvent) at 20℃; for 24h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

72
[ 769-78-8 ]
[ 102-49-8 ]
[ 65609-04-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	In neat (no solvent) at 20℃; for 24h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

73
[ 2620-50-0 ]
[ 769-78-8 ]
[ 65609-38-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	In neat (no solvent) at 20℃; for 24h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

74
[ 27757-85-3 ]
[ 769-78-8 ]
[ 4595-96-4 ]

Yield	Reaction Conditions	Operation in experiment
48%	In neat (no solvent) at 20℃; for 24h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

75
[ 617-89-0 ]
[ 769-78-8 ]
[ 3952-30-5 ]

Yield	Reaction Conditions	Operation in experiment
50%	In neat (no solvent) at 20℃; for 24h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

76
[ 769-78-8 ]
[ 64-04-0 ]
[ 3278-14-6 ]

Yield	Reaction Conditions	Operation in experiment
69%	In neat (no solvent) at 20℃; for 24h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

77
[ 769-78-8 ]
[ 156-41-2 ]
[ 3418-95-9 ]

Yield	Reaction Conditions	Operation in experiment
69%	In neat (no solvent) at 20℃; for 24h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

78
[ 769-78-8 ]
[ 2975-41-9 ]
[ 53545-57-6 ]

Yield	Reaction Conditions	Operation in experiment
55%	In neat (no solvent) at 20℃; for 24h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

79
[ 769-78-8 ]
[ 108-91-8 ]
[ 1759-68-8 ]

Yield	Reaction Conditions	Operation in experiment
53%	In neat (no solvent); at 20℃; for 48h;Green chemistry;	General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Synthetic Communications,2014,vol. 44,p. 2364 - 2376

80
[ 769-78-8 ]
[ 7568-93-6 ]
[ 34119-82-9 ]

Yield	Reaction Conditions	Operation in experiment
63%	In neat (no solvent) at 20℃; for 24h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

81
[ 13054-87-0 ]
[ 769-78-8 ]
[ 13973-26-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	In neat (no solvent) at 20℃; for 24h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

82
[ 2038-03-1 ]
[ 769-78-8 ]
[ 4476-13-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	In neat (no solvent) at 20℃; for 0.666667h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

83
[ 3731-53-1 ]
[ 769-78-8 ]
[ 3820-26-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	In neat (no solvent) at 20℃; for 24h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

84
[ 2706-56-1 ]
[ 769-78-8 ]
[ 4976-05-0 ]

Yield	Reaction Conditions	Operation in experiment
73%	In neat (no solvent) at 20℃; for 24h; Green chemistry;	PREPARATION OF THE BENZAMIDES General procedure: In a round-bottomed flask, a mixture of a suitable amine (1 eq.) and 3 eq. of vinyl benzoate were stirred at room temperature for 24 hours. The evolution of the reaction was monitored by TLC. After complete consumption of the amine, the crude reaction mixture was concentrated in vacuo and purified by flash chromatography on silica gel (CH2Cl2 as eluent) or by crystallization using Hexane as the crystallisation solvent to gave the pure benzamides.

Reference： [1]Alalla, Affef; Merabet-Khelassi, Mounia; Aribi-Zouioueche, Louisa; Riant, Olivier [Synthetic Communications, 2014, vol. 44, # 16, p. 2364 - 2376]

85
[ 105-38-4 ]
[ 65-85-0 ]
[ 769-78-8 ]

Yield	Reaction Conditions	Operation in experiment
77%	With 1,10-Phenanthroline; palladium diacetate at 140℃; for 1.25h;	9 For the performance of the examples which follow, the experimental setup according to FIG. 1 was used. In the reservoir vessel (3), vinyl acetate (examples 1-7, 15-22) or vinyl propionate (Examples 8-14) conducted in via line (1), the starting carboxylic acid R-C(O)OH to be vinylated via line (2), and catalyst solution via line (23) were mixed and pumped via line (4) to the reaction vessel (5) configured as a flow tube. The liquid reaction mixture withdrawn via line (6) was decompressed to standard pressure in the decompression vessel (7). Gaseous components formed, which comprised vinyl acetate or vinyl propionate and acetic acid or propionic acid formed, were drawn off via line (8). The liquid output removed via, line (9) was analysed by gas chromatography. [0059] The starting carboxylic acids R-C(O)OH used for transvinylation, the reaction conditions established in the reaction vessel (5) and the space-time, yields of the desired vinyl esters R-C(O)OCH═CH determined in the gas chromatography analysis are compiled in Tables 1 to 7 below. The catalyst solution was prepared by blending the palladium acetate Pd(OAc)2 catalyst precursor with the bidentate nitrogen ligands 1,10-phenanthroline (Examples 1-16, 21-24) or 2,2′-bipyridyl (Examples 17, 16) in a mixture of vinyl acetate or vinyl propionate and the respective starting carboxylic acid. In Examples 19 and 20, the [Ru(CO)2OAc]n complex was used as the catalyst precursor. In Examples 21-23, based on the molar carboxylic acid input, vinyl acetate was used in a molar deficiency. The active catalyst was formed in the reaction vessel under reaction conditions. The molar ratio stated for the catalyst precursor is based on mol of palladium or mol of ruthenium. The isononanoic acid used was based on the hydroformylation of diisobutylene with subsequent oxidation of the corresponding aldehyde and contained predominantly 3,5,5-trimethylhexenoic acid.

Reference： [1]Current Patent Assignee: Oman Oil Company (in: Government of Oman); GOVERNMENT OF OMAN - US2014/357881, 2014, A1 Location in patent: Paragraph 0058-0059

86
[ 769-78-8 ]
C₁₆H₂₀Co₂O₇Si [ No CAS ]
2-(2-[tert-butyl(dimethyl)silyl]oxy}ethyl)cyclopent-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With 4-methylmorpholine N-oxide at 25℃; for 16h; Inert atmosphere;	2 Enone 71: Enone 71: To a stirred solution of cobalt alkyne complex 102 (1.10 g, 3.10 mmol, 1.0 equiv) at 25 °C in vinyl benzoate (20.0 mL, 202 mmol, 65 equiv) was added a solution of ΝΜΟ0 (2.50 g, 18.9 mmol, 6.1 equiv) in CH2CI2 (35 mL) via addition funnel over 1 h. After stirring for 15 h at this temperature the crude reaction mixture was filtered through a short column (S1O2, Et20) and the filtrate was concentrated under reduced pressure. Purification by flash column chromatography (S1O2, hexane:Et20, 9.5:0.5→ 7:3) to give pave pure title compound (71, 0.46 g, 1.91 mmol, 62% yield). 71 : f = 0.17 (hexane:Et20, 9: 1); IR (film): vmax = 2954, 2928, 2856, 1703, 1251, 1098 cm"1; NM (600 MHz, CDCI3) δ 7.44 - 7.37 (m, 1 H), 3.69 (t, J = 6.4 Hz, 2 H), 2.55 (dq, J = 4.5, 2.2 Hz, 2 H), 2.37 (ddd, J = 12.3, 5.8, 3.8 Hz, 4 H), 0.85 (s, 9 H), 0.00 ppm (s, 6 H); 13C NMR (150 MHz, CDC13) δ 209.85, 159.42, 143.28, 61.04, 34.36, 28.34, 26.65, 25.88, 18.25, -5.34 ppm; HR- MS (ESI-TOF): calcd for Ci3H2502Si+ [M+H]+: 241.1618, found: 241.1607.
62%	With water; 4-methylmorpholine N-oxide In dichloromethane at 25℃; for 16h; Inert atmosphere;

Reference： [1]Current Patent Assignee: WILLIAM MARSH RICE UNIVERSITY - WO2015/48268, 2015, A1 Location in patent: Page/Page column 155; 156
[2]Nicolaou; Pulukuri, Kiran Kumar; Rigol, Stephan; Heretsch, Philipp; Yu, Ruocheng; Grove, Charles I.; Hale, Christopher R. H.; ElMarrouni, Abdelatif; Fetz, Verena; Brönstrup, Mark; Aujay, Monette; Sandoval, Joseph; Gavrilyuk, Julia [Journal of the American Chemical Society, 2016, vol. 138, # 20, p. 6550 - 6560]

87
[ 769-78-8 ]
[ 135-19-3 ]
[ 93-44-7 ]

Reference： [1]New Journal of Chemistry,2015,vol. 39,p. 8329 - 8336

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CAS No. :	769-78-8	MDL No. :	MFCD00048141
Formula :	C₉H₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KOZCZZVUFDCZGG-UHFFFAOYSA-N
M.W :	148.16	Pubchem ID :	13037
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P321
P322
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P353	Rinse skin with water/shower.
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P378
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
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P406	Store in corrosive resistant/ container with a resistant inner liner.
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P411
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P413
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P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
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P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
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H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ 769-78-8 ] Synthesis Path-Downstream 1~87

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